In this Stork enamine reaction, cyclohexanone is reacted with pyrrolidine in the presence of p-TsOH catalysis to produce an enamine. This enamine undergoes.

Author: Mezirisar Dulkree
Country: Sri Lanka
Language: English (Spanish)
Genre: Love
Published (Last): 18 February 2016
Pages: 481
PDF File Size: 17.95 Mb
ePub File Size: 8.50 Mb
ISBN: 432-2-40788-424-1
Downloads: 78637
Price: Free* [*Free Regsitration Required]
Uploader: Maushakar

Oh no, there’s been an error

Organic Chemistry Hardcover 6th ed. The Stork enamine alkylationinvolves the addition of an enamine to an alpha, beta-unsaturated carbonyl acceptor in a process similar to the Michael reaction.

Views Read Edit View history. The end product is a 1,5 dicarbonyl compound. Enamines act as nucleophiles in a fashion similar to enolates. Formation of an enamine Step 2: Because of this enamines can be used as synthetic equivalents as enolates in many reactions.

Illustrated Glossary of Organic Chemistry – Stork enamine reaction

The imine is then reacted with an Grignard reagent to the corresponding magnesium salt to an intermediate capable of displacing a halide. Steven Farmer Sonoma State University.


As previously seen, aldehydes and ketones react with 2 o amines to reversibly form enamines. Alkylation of an Enamine Enamined undergo an S N 2 reaction with reactive alkyl halides to give the iminium salt. Reactions, Mechanisms, and Structure 3rd ed. In a special case of this reaction type it is also possible to alkylate ketones or aldehydes with alkyl halides as less reactive electrophiles: This page was last edited on 6 Aprilat By using this site, you agree to the Terms of Use and Privacy Policy.

Some of the advantages of using an enamine over and enolate are enamines are neutral, easier to prepare, and usually prevent the overreaction problems plagued by enolates. Hydrolysis once again yields the alkylated ketone. Enamined undergo an S N 2 reaction with reactive alkyl halides to give the iminium salt. In this method a carbonyl compound is converted to an imine by alkylimino-de-oxo-bisubstitution with a primary amine. Carbon-carbon bond forming reactions Name reactions. Retrieved from ” https: The iminium salt can be hydrolyzed back into the carbonyl.


Enamine Reactions

This process requires a three steps: Use dmy dates from June From Wikipedia, the free encyclopedia. Michael Addition using Enamines Enamines, like other weak bases, add 1,4 to enones. In other projects Wikimedia Commons.

These reactions are generally known as the Stork enamine reaction after Gilbert Stork of Columbia University who originated the work.

When the electrophile is an acyl halidea 1,3- diketone is formed Stork acylation.

Enamines, like other weak bases, add 1,4 to enones.

Back To Top